N⁽²⁾-(2-nitrobenzylcarbonyl)-O⁽⁶⁾-(2-chloroethyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine

Base Information

• Chemical Name: N⁽²⁾-(2-nitrobenzylcarbonyl)-O⁽⁶⁾-(2-chloroethyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine
• CAS No.: 1376827-49-4
• Molecular Formula: C₃₂H₄₉ClN₆O₈Si₂
• Molecular Weight: 737.4

Synonyms:N⁽²⁾-(2-nitrobenzylcarbonyl)-O⁽⁶⁾-(2-chloroethyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine

Chemical Property of N⁽²⁾-(2-nitrobenzylcarbonyl)-O⁽⁶⁾-(2-chloroethyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁽²⁾-(2-nitrobenzylcarbonyl)-O⁽⁶⁾-(2-chloroethyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine

There total 9 articles about N⁽²⁾-(2-nitrobenzylcarbonyl)-O⁽⁶⁾-(2-chloroethyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 51.0%

N(2)-(2-nitrobenzylcarbonyl)-O(6)-(2-hydroxyethyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine (1376827-48-3) → N(2)-(2-nitrobenzylcarbonyl)-O(6)-(2-chloroethyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine (1376827-49-4)

Guidance literature:

N⁽²⁾-(2-nitrobenzylcarbonyl)-O⁽⁶⁾-(2-hydroxyethyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine; With triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 0.25h;

With trichloroacetonitrile; In tetrahydrofuran; at 0 ℃; for 0.333333h;

DOI:10.1002/anie.201108018

Reference yield:

2-nitrobenzylcarbonylimidazole → N(2)-(2-nitrobenzylcarbonyl)-O(6)-(2-chloroethyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine (1376827-49-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 18-crown-6 ether; sodium hydride / tetrahydrofuran / 0.17 h / 20 °C

1.2: 3 h / 20 °C

2.1: dmap; triethylamine / dichloromethane / 3 h / 0 °C

3.1: Quinuclidine / tetrahydrofuran / 1 h / 20 °C

3.2: 3 h / 0 °C

4.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C

4.2: 0.33 h / 0 °C

With Quinuclidine; dmap; 18-crown-6 ether; sodium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.1002/anie.201108018

Reference yield:

2'-Deoxyguanosine (961-07-9) → N(2)-(2-nitrobenzylcarbonyl)-O(6)-(2-chloroethyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine (1376827-49-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / -10 - 20 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / -20 - 20 °C

3.1: 18-crown-6 ether; sodium hydride / tetrahydrofuran / 0.17 h / 20 °C

3.2: 3 h / 20 °C

4.1: dmap; triethylamine / dichloromethane / 3 h / 0 °C

5.1: Quinuclidine / tetrahydrofuran / 1 h / 20 °C

5.2: 3 h / 0 °C

6.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C

6.2: 0.33 h / 0 °C

With Quinuclidine; 1H-imidazole; dmap; 18-crown-6 ether; sodium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.201108018

upstream raw materials:

N⁽²⁾-(2-nitrobenzylcarbonyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine

N⁽²⁾-(2-nitrobenzylcarbonyl)-O⁽⁶⁾-(2,4,6-triisopropylphenylsulfonyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine

N⁽²⁾-(2-nitrobenzylcarbonyl)-O⁽⁶⁾-(2-hydroxyethyl)-5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine

5'-O-tert-butyldimethylsilyl-3'-O-triethylsilyl-2'-deoxyguanosine

Downstream raw materials:

N⁽²⁾-(2-nitrobenzylcarbonyl)-O⁽⁶⁾-(2-chloroethyl)-2'-deoxyguanosine

N⁽²⁾-(2-nitrobenzylcarbonyl)-O⁽⁶⁾-(2-chloroethyl)-5'-O-dimethoxytrityl-2'-deoxyguanosine

N⁽²⁾-(2-nitrobenzylcarbonyl)-O⁽⁶⁾-(2-chloroethyl)-5''-O-dimethoxytrityl-3'-O-(2-cyanoethyl-N,N-diisopropylphosphoramidite)-2'-deoxyguanosine

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